Ethylene Glycol → Ethyl 2-(2-ethyl-1,3-dioxolan-2-yl)acetate

HRID 31654

반응식

HRID 31654 반응식
[O:1]=[C:2]([CH2:9][CH3:10])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:11](O)[CH2:12][OH:13].C(OCC)(OCC)OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)(=O)C.CCCCCCC>[CH2:7]([O:6][C:4](=[O:5])[CH2:3][C:2]1([CH2:9][CH3:10])[O:13][CH2:12][CH2:11][O:1]1)[CH3:8]

참가 물질

7

반응물 4

HCID 174Ethylene GlycolHCID 31214Ethyl orthoformateHCID 78656Ethyl 3-oxovalerateHCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 14244230Ethyl 2-(2-ethyl-1,3-dioxolan-2-yl)acetate수율 58.9%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 8900Heptane용매

실험 절차

A mixture of ethyl 3-oxopentanoate (5 g, 34.7 mmol), ethylene glycol (10.8 g, 174 mmol), triethyl orthoformate (5.14 g, 34.7 mmol), and p-toluenesulfonic acid monohydrate (598 mg, 3.14 mmol) was stirred at room temperature overnight. To the reaction mixture, heptane and ethyl acetate were added to dilute solution, which was washed with water. The organic layer was washed with a saturated saline solution, dried over magnesium sulfate, filtrated and the filtrate was concentrated under reduced pressure. The residue was dissolved in heptane and subjected to NH silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/0→10/1) to obtain the title compound (3.85 g, yield: 58.9%) as colorless oil.

후처리

  1. washwas washed with water
  2. washThe organic layer was washed with a saturated saline solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in heptane
  7. washsubjected to NH silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/0→10/1)

출처 및 근거

ORD 기록
ord-0f477811c9694e35a09ec124018f0987
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425634B2

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